Hey @Brendan Ferguson - I am friends with several other Chicago firefighters who are in real estate. 

You will have a higher risk running into DTI issue that route as well.

Hi Christine, You need what's called a builders risk policy. 

It was one out of several properties we invested in.

HOWEVER:This higher income type of property investment comes with higher risk.

Some facts of the house:Location: Nassau County, NY, Town of HempsteadYear built:1929Purchase price: 290,000 in 2013Condition: AverageLot size sqft: 5000Livable sqft: 760I'm seeing several houses in my zip code that have been demolished and rebuilt into new houses with the maximum allowable livable square footage selling between $1.0M- 1.2M.Which is a better option taking into consideration, profit and capital gain tax (assuming my household income of 80K)1) Should I sell this house as is at $450K2) Demolish this house and rebuild it without taking out a loan.

@Ethan Reay several people mentioned matterport, which I have not used.

Be wary of overly creative write-off strategies, as the IRS isn't easily fooled, risking audits and hefty penalties.

Yeah, that is STR’s risk factor.

Hi Jane,I would not say that the decision to create an entity or not comes down to the number of properties that you own specifically but will more likely be based on your risk aversion.